1. Round | 07/08/1999 | Walsall FC | - | Swindon Town | 0:0 | ||||
10. Round | 02/10/1999 | Swindon Town | - | Bolton Wanderers | 0:4 | ||||
11. Round | 09/10/1999 | Swindon Town | - | Stockport County | 1:1 | ||||
12. Round | 16/10/1999 | Fulham FC | - | Swindon Town | 1:0 | ||||
13. Round | 19/10/1999 | Barnsley FC | - | Swindon Town | 1:0 | ||||
14. Round | 23/10/1999 | Swindon Town | - | Sheffield United | 2:2 | ||||
15. Round | 26/10/1999 | Swindon Town | - | Port Vale FC | 2:1 | ||||
16. Round | 30/10/1999 | Bolton Wanderers | - | Swindon Town | 2:0 | ||||
22. Round | 04/12/1999 | Swindon Town | - | Walsall FC | 1:1 | ||||
23. Round | 18/12/1999 | Manchester City | - | Swindon Town | 3:0 |